Sodium Carbonate → HCID 58356438, compound

HRID 244727Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:12]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[O:13])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.[NH:32]1[C:40]2[C:35](=[CH:36][C:37](B(O)O)=[CH:38][CH:39]=2)[CH:34]=[CH:33]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[NH:32]1[C:40]2[C:35](=[CH:36][C:37]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][NH:8]4)=[C:4]([NH:11][C:12]([C:14]4[N:15]=[C:16]([CH3:19])[S:17][CH:18]=4)=[O:13])[CH:3]=3)=[CH:38][CH:39]=2)[CH:34]=[CH:33]1

Participants

Conditions

Temperature: 150 °C

Procedure

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (50 mg), Pd(dppf)Cl2 (12 mg), 2M sodium carbonate (0.222 ml), 1,4-dioxane (1 ml) and water (1 ml) were added to 1H-indol-5-ylboronic acid (29 mg) in a microwave vial. The vial was sealed and heated under microwave irradiation at 150° C. for 15 min. The reaction mixture was extracted with DCM (2×20 ml) and then separated, combined organic layers were evaporated to dryness. The residue was dissolved in methanol:DMSO (1 ml, 1:1) and purified by mass directed preparative HPLC (Method A) to give title compound (3.7 mg).

Workup

customThe vial was sealed
extractionThe reaction mixture was extracted with DCM (2×20 ml)
customseparated
customwere evaporated to dryness
dissolutionThe residue was dissolved in methanol
customDMSO (1 ml, 1:1) and purified by mass

Sources & evidence

ORD record: ord-7b17b1daa6ce4b028541c08ec1815db3
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658635B2

Reaction notes

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